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Frankly, my self-esteem was so low until only a few years ago, I never would have expected anything but a no (in high school, I was that loner kid that everyone hated), so I never saw the point in asking.
Tho I did try asking my best friend out once and I got shot down. As it turns out, he's gay, but I didn't know back then, and it killed what little self-confidence I had at the time and I never dared to try that again.
Fortunately, I'm finally in a relationship where I'm not shy about asking for what I want.
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